EP1852456B1 - Procédé pour la préparation de composés organosiliciques ß-cetocarbonyl-fonctionnalisé - Google Patents

Procédé pour la préparation de composés organosiliciques ß-cetocarbonyl-fonctionnalisé Download PDF

Info

Publication number
EP1852456B1
EP1852456B1 EP07106503A EP07106503A EP1852456B1 EP 1852456 B1 EP1852456 B1 EP 1852456B1 EP 07106503 A EP07106503 A EP 07106503A EP 07106503 A EP07106503 A EP 07106503A EP 1852456 B1 EP1852456 B1 EP 1852456B1
Authority
EP
European Patent Office
Prior art keywords
radical
organosilicon compounds
integer
general formula
ketocarbonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
EP07106503A
Other languages
German (de)
English (en)
Other versions
EP1852456A1 (fr
Inventor
Christian Herzig
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP1852456A1 publication Critical patent/EP1852456A1/fr
Application granted granted Critical
Publication of EP1852456B1 publication Critical patent/EP1852456B1/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0889—Reactions not involving the Si atom of the Si-O-Si sequence
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups

Definitions

  • the invention relates to a process for the preparation of ⁇ -ketocarbonyl-functional organosilicon compounds. Furthermore, the invention relates to ⁇ -ketocarbonyl-functional organosilicon compounds.
  • Polymeric ⁇ -ketoester siloxanes are made US 4,808,649 known, as well as a process for their preparation and their use as a stabilizer for polyvinyl chloride.
  • the organosilicon compounds (1) may be monomeric, oligomeric or polymeric and may have a linear, branched or cyclic structure.
  • radicals R are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n Pentyl, iso-pentyl, neo-pentyl, tert-pentyl, hexyl, such as the n -hexyl, heptyl, such as the n-heptyl, octyl, such as the n-octyl and iso-octyl, such as 2 2,4-trimethylpentyl radical, nonyl radicals such as the n-nonyl radical, decyl radicals such as the n-decyl radical, dodecyl radicals such as the n-dodecyl radical, and octadecyl radicals such as the n-octa
  • radicals R 1 are alkylene radicals having 1 to 18 carbon atoms, such as radicals of the formula -CH 2 -, -CH 2 CH 2 -, -CH (CH 3 ) -, -CH 2 CH 2 CH 2 -, -CH 2 C- (CH 3 ) H, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH (CH 3 ) -, wherein -CH 2 CH 2 - and -CH 2 CH 2 CH 2 - are preferred.
  • radicals A are -CH 2 -NH 2 -CH (CH 3 ) -NH 2 -C (CH 3 ) 2 -NH 2 -CH 2 CH 2 -NH 2 -CH 2 CH 2 CH 2 -NH 2 -CH 2 CH 2 CH 2 CH 2 -NH 2 -CH 2 CH 2 CH (CH 3 ) -NH 2 -CH 2 CH 2 CH 2 -NH-CH 2 CH 2 CH 2 -N (CH 3 ) -CH 2 CH 2 -NH 2 -CH 2 CH 2 CH 2 [-NH-CH 2 CH 2 ] 2 -NH 2 -CH 2 CH 2 C (CH 3 ) 2 CH 2 -NH 2 .
  • hydrocarbon radicals R also apply to hydrocarbon radicals R 2 .
  • alkyl radicals R 3 are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl , n-pentyl, iso-pentyl, neo-pentyl, tert-pentyl, hexyl, such as the n-hexyl, heptyl, such as the n-heptyl, octyl, such as the n-octyl and iso-octyl, such as the 2,2,4-trimethylpentyl radical.
  • alkyl radicals such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl , n-pentyl, iso-
  • the organosilicon compounds (1) used in the process according to the invention preferably have a viscosity of 1 mPa.s to 1 000 000 mPa.s at 25 ° C, preferably 100 mPa.s to 50 000 mPa.s at 25 ° C and have a Molecular weight M n of preferably 200 to 200,000 daltons, preferably 2,000 to 50,000 daltons.
  • the organosilicon compounds (1) contain primary and optionally secondary amino groups in titratable amounts of 0.01 to 12 meq / g, particularly preferably in the range of 0.05 to 3 meq / g of organosilicon compound (1).
  • organosilicon compounds (1) One type of organosilicon compounds (1) or several types of organosilicon compounds (1) can be used.
  • organic ester compounds (2) are propiolactone, butyrolactone, caprolactone, ethylene carbonate, propylene carbonate, butylene carbonate and glycerol carbonate.
  • ester compounds (2) are preferably used in approximately stoichiometric amount based on the sum of all the primary amino groups present in (1). In the process according to the invention, therefore, ester compounds (2) are preferably used in amounts of 1.0 to 2.0 mol, preferably 1.0 to 1.2 mol, per mol of primary amino group -NH 2 in organosilicon compounds (1).
  • the 1st stage of the process according to the invention is preferably carried out at a temperature of 10 to 120 ° C, preferably 25 to 80 ° C. If the ester compounds (2) in the organosilicon compounds (1) are not or only slightly soluble, a higher reaction temperature of 50 to 100 ° C is preferred.
  • the progress of the reaction in the first stage of the process according to the invention can be recognized by the clarification of an initially turbid mixture.
  • the remainder B contains urethanecarbinol groups by the reaction of (1) with (2).
  • hydrocarbon radicals R also apply to hydrocarbon radicals R 5 .
  • Preferred is diketene of the formula used.
  • diketene derivatives such as diketene-acetone adduct or t-butyl acetoacetate, which release diketene again at elevated temperature.
  • the amount of diketene (3) with which the reaction products of (1) and (2) are reacted can be selected within wide limits. If the organosilicon compounds (1) contain not only primary amino groups but also secondary amino groups, at least the amounts of diketene (3) equivalent to these primary and secondary amino groups are preferably used.
  • the carbinol groups formed from the reaction of (1) with (2) may be wholly or partly diketenes (3) be implemented. For this purpose, a slight excess of diketenes (3) may be advantageous, which is preferably removed in vacuo again after completion of the reaction (volatile diketene) or otherwise reacted.
  • diketenes (3) are preferably used in amounts of 0.5 to 1.25 mol, preferably 0.8 to 1.1 mol, per mol of the sum of secondary amino groups (secondary -NH-). and carbinol group used in the reaction products of (1) and (2).
  • a particular embodiment of the invention is the gleichmolare use of diketene and amino and carbinol, ie diketene (3) is particularly preferably in amounts of about 1.0 mole per mole of secondary amino group and carbinol in the reaction products of (1) and (2 ) used.
  • the reaction of diketene (3) with the secondary amino groups in the reaction product of (1) with (2) preferably proceeds spontaneously at ambient temperature, but can also be carried out at elevated temperatures.
  • elevated temperature is required; The reaction is therefore preferably carried out at a temperature of 50 to 120 ° C.
  • the reaction with diketenes (3) in the second stage of the process according to the invention is preferably carried out in the presence of basic catalysts, such as tert. Amines, performed.
  • basic catalysts such as tert. Amines
  • tert. Amines are triethylamine, trinonylamine, tris (isotridecylamine), diazabicyclooctane, tetramethylethylenediamine, pentamethyldiethylenetriamine, pentamethyldipropylenetriamine and bis (dimethylaminopropyl) aminoethanol.
  • the process according to the invention is preferably carried out at the pressure of the surrounding atmosphere, ie at about 1020 hPa, but it can also be carried out at higher or lower pressures.
  • the process according to the invention can be carried out batchwise, semicontinuously or continuously.
  • the preparation of the ⁇ -ketocarbonyl-functional organosilicon compounds according to the invention can be carried out in organic solvents, in particular at high viscosities of the organosilicon compounds according to the invention, this can be advantageous.
  • solvents are saturated hydrocarbons, such as n-pentane, n-hexane, n-heptane and n-octane, and their branched isomers, benzines, eg.
  • alkane mixtures having a boiling range of 80 ° C to 140 ° C at 1020 hPa, unsaturated hydrocarbons such as 1-hexene, 1-heptene, 1-octene and 1-decene, aromatic hydrocarbons such as benzene, toluene and xylenes, halogenated alkanes with 1 to 6 carbon atoms, such as methylene chloride, trichlorethylene and perchlorethylene, ethers, such as di-n-butyl ether, alcohols, such as methanol, ethanol, n-propanol and iso-propanol, and low molecular weight linear and cyclic organopolysiloxanes.
  • unsaturated hydrocarbons such as 1-hexene, 1-heptene, 1-octene and 1-decene
  • aromatic hydrocarbons such as benzene, toluene and xylenes
  • radicals R 2 apply in their entirety to radicals R 2 ' except that R 2' does not denote a hydrogen atom.
  • At least 80 mole%, preferably at least 90 mole%, of the ⁇ -ketocarbonyl-functional organosilicon compounds y is 1.
  • ⁇ -Ketocarbonyl-functional organosilicon compounds have a molecular weight M n of preferably 400 to 200,000 daltons, preferably 2,000 to 100,000 daltons.
  • the reaction mixture is cooled. This gives a clear, yellowish oil with a viscosity of 554 mm 2 / s (25 ° C). Amine groups can no longer be detected ( ⁇ 0.001 meq / g).
  • the 1 H-NMR spectrum confirms the quantitatively obtained acetylacetoxyethyl urethane groups.
  • the product contains about 0.8 wt .-% unused ethylene carbonate, which can be removed in vacuo at 120 ° C.
  • Example 2 The procedure of Example 2 is repeated with the modification that the 1st stage of the process, the reaction with ethylene carbonate, is not carried out. After diketene is added, the previously slightly liquid oil is gelatinized in less than 1 minute.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)

Claims (10)

  1. Procédé de préparation de composés d'organosilicium à fonction β-cétocarbonyle, dans lequel
    lors d'une première étape,
    (1) des composés d'organosilicium contenant au moins un radical organique relié à SiC comportant un groupe amino primaire sont mis en réaction avec
    (2) des composés esters organiques, de préférence des carbonates organiques cycliques et des lactones, contenant un groupe de formule

            -O-C(=O)-

    et, lors d'une seconde étape
    les produits de la réaction de (1) et (2) obtenus lors de la première étape sont ensuite mis en réaction avec
    (3) des dicétènes ou des dérivés de dicétènes.
  2. Procédé selon la revendication 1, dans lequel des composés d'organosilicium contenant au moins un radical organique A relié à SiC de formule générale

            -R1(-NR2-R1)x-NH2     (I)

    dans laquelle
    R1 est un radical organique bivalent comportant 1 à 18 atomes de carbone,
    R2 est un atome d'hydrogène ou un radical organique monovalent comportant 1 à 18 atomes de carbone,
    x est 0 ou un entier de 1 à 10, de préférence 0, 1 ou 2,
    sont utilisés en tant que composés d'organosilicium (1).
  3. Procédé selon la revendication 1 ou 2, dans lequel des organopolysiloxanes comprenant des unités de formule générale A a ⁢ R b OR 3 SiO c 4 - a + b + c 2
    Figure imgb0014
    dans laquelle A est tel que défini ci-dessus,
    R est un radical hydrocarboné monovalent, substitué ou non substitué, comportant 1 à 18 atomes de carbone par radical,
    R3 est un atome d'hydrogène ou un radical alkyle comportant 1 à 8 atomes de carbone,
    a est 0 ou 1,
    b est 0, 1, 2 ou 3 et
    c est 0 ou 1,
    à condition que la somme a+b+c soit ≤ 3 et qu'en moyenne au moins un radical A soit présent par molécule,
    sont utilisés en tant que composés d'organosilicium (1).
  4. Procédé selon l'une quelconque des revendications 1 à 3, dans lequel des organopolysiloxanes des formules générales

            AgR3-gSiO(SiR2O)l(SiRAO)kSiR3-gAg     (IIIa)

    ou

            (R3O)R2SiO(SiR2O)n(SiRAO)mSiR2(OR3)     (IIIb)

    dans lesquelles A, R et R3 sont tels que définis ci-dessus,
    g est 0 ou 1,
    k est 0 ou un entier de 1 à 30 et
    l est 0 ou un entier de 1 à 1 000,
    m est un entier de 1 à 30 et
    n est 0 ou un entier de 1 à 1 000,
    à condition qu'en moyenne au moins un radical A soit présent par molécule,
    sont utilisés en tant que composés d'organosilicium (1).
  5. Procédé selon l'une quelconque des revendications 1 à 4, dans lequel des lactones ou des cyclocarbonates de formule générale
    Figure imgb0015
     dans laquelle R4 est un radical hydrocarboné bivalent ou trivalent qui comprend 1 à 18 atomes de carbone et peut être interrompu par un ou plusieurs atomes d'oxygène séparés,
    v est 0 ou 1 et
    z est 1 ou 2,
    sont utilisés en tant que composés esters organiques (2).
  6. Procédé selon l'une quelconque des revendications 1 à 5, dans lequel des dicétènes de formule générale
    Figure imgb0016
     dans laquelle
    R5 est un atome d'hydrogène ou un radical hydrocarboné comportant 1 à 18 atomes de carbone,
    sont utilisés en tant que dicétènes (3).
  7. Composé d'organosilicium à fonction β-cétocarbonyle contenant au moins un radical organique G relié à SiC choisi dans le groupe constitué des radicaux G1 et G2, G1 étant un radical de formule générale

            -R1{-N[C(=O)-CHR5-C(=O)-CH2R5]-R1}x-NH-C(=O)-(O)v-R4{-O[-C(=O)-CHR5-C(=O)-CHR5]y-H}z     (VIII)

    et G2 est un radical de formule générale

            -R1(-NR2'-R1)x-NH-C(=O)-(O)v-R4{-O[-C(=O)-CHR5-C(=O)-CHR5]y-H}z     (IX),

    dans lesquelles R1, R2, R4, R5, v et x sont tels que définis dans les revendications 2, 5 et 6, R2' a une des significations de R2 à condition que R2' ne soit pas un atome d'hydrogène,
    R2' est un radical organique monovalent comportant 1 à 18 atomes de carbone,
    y est 0 ou 1,
    z est 1 ou 2,
    à condition que y soit 1 dans au moins une partie des composés d'organosilicium à fonction β-cétocarbonyle.
  8. Composé d'organosilicium à fonction β-cétocarbonyle selon la revendication 7, dans lequel R4 est un radical de formule -CH2CH2-, R5 est un atome d'hydrogène, v est 1 et z est 1.
  9. Composé d'organosilicium à fonction β-cétocarbonyle selon la revendication 7 ou 8, qui est un organopolysiloxane comportant des unités de formule générale G a ⁢ R b OR 3 SiO c 4 - a + b + c 2
    Figure imgb0017
    dans laquelle G est un radical choisi dans le groupe constitué des radicaux G1 et G2, G1 et G2 étant tels que définis dans la revendication 7 et
    R, R3, a, b et c sont tels que définis dans la revendication 3,
    à condition que la somme a+b+c soit ≤ 3 et qu'en moyenne au moins un radical G soit présent par molécule.
  10. Composé d'organosilicium à fonction β-cétocarbonyle selon la revendication 7, 8 ou 9, qui est un organopolysiloxane de formule générale

            GgR3-gSiO(SiR2O)l(SiRGO)kSiR3-gGg     (IIIa)

    ou

            (R3O)R2SiO(SiR2O)n(SiRCO)mSiR2(OR3)     (IIIb)

    dans laquelle G, R et R3 sont tels que définis dans la revendication 8,
    g est 0 ou 1,
    k est 0 ou un entier de 1 à 30 et
    l est 0 ou un entier de 1 à 1 000,
    m est un entier de 1 à 30 et
    n est 0 ou un entier de 1 à 1 000,
    à condition qu'en moyenne au moins un radical G soit présent par molécule.
EP07106503A 2006-05-04 2007-04-19 Procédé pour la préparation de composés organosiliciques ß-cetocarbonyl-fonctionnalisé Expired - Fee Related EP1852456B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102006020815A DE102006020815A1 (de) 2006-05-04 2006-05-04 Verfahren zur Herstellung von beta-Ketocarbonyl-funktionellen Organosiliciumverbindungen

Publications (2)

Publication Number Publication Date
EP1852456A1 EP1852456A1 (fr) 2007-11-07
EP1852456B1 true EP1852456B1 (fr) 2009-06-17

Family

ID=38353834

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07106503A Expired - Fee Related EP1852456B1 (fr) 2006-05-04 2007-04-19 Procédé pour la préparation de composés organosiliciques ß-cetocarbonyl-fonctionnalisé

Country Status (6)

Country Link
US (1) US7495119B2 (fr)
EP (1) EP1852456B1 (fr)
JP (1) JP5044276B2 (fr)
KR (1) KR100936414B1 (fr)
CN (1) CN101067024B (fr)
DE (2) DE102006020815A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006039940A1 (de) * 2006-08-25 2008-03-06 Wacker Chemie Ag ß-Ketocarbonyl-funktionelle Siloxanpolymere enthaltende Zusammensetzungen
JP5160921B2 (ja) * 2008-02-25 2013-03-13 花王株式会社 ウレタン結合含有基を有するオルガノポリシロキサン化合物
DE102008000931A1 (de) * 2008-04-02 2009-10-08 Wacker Chemie Ag Wachsartige ß-Ketocarbonyl-funktionelle Organosiliciumverbindungen
JP2011522944A (ja) * 2008-06-13 2011-08-04 クラリアント・ファイナンス・（ビーブイアイ）・リミテッド カルバマート官能基を有するポリジオルガノシロキサン、それらの調製、および繊維工業における柔軟剤としてのそれらの使用
EP1972330B1 (fr) * 2008-06-13 2012-09-12 Clariant Finance (BVI) Limited Compositions cosmétiques ou pharmaceutiques comportant des polysiloxanes modifiés avec un groupe carbamate
JP2016501925A (ja) 2012-10-29 2016-01-21 スリーエム イノベイティブ プロパティズ カンパニー ポリジオルガノシロキサンポリウレタン
KR102296683B1 (ko) * 2016-11-16 2021-09-01 와커 헤미 아게 Ｂ-케토카르보닐-작용성 오르가노실리콘 화합물의 분산액
US11597840B2 (en) * 2017-12-06 2023-03-07 Wacker Chemie Ag Emulsions of beta-ketocarbonyl-functional organosilicon compounds

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2602776B1 (fr) * 1986-08-12 1988-11-10 Rhone Poulenc Chimie Diorganopolysiloxane a fonction beta-cetoester utile comme stabilisant des polymeres a base de polychlorure de vinyle
JPS63313793A (ja) * 1987-06-15 1988-12-21 Nippon Paint Co Ltd 金属キレ−ト化合物
JP2693482B2 (ja) * 1988-05-12 1997-12-24 日本ペイント株式会社 硬化性組成物
US4973680A (en) * 1989-03-03 1990-11-27 National Starch And Chemical Investment Holding Corporation Organosiloxane-containing polysaccharides
GB9101205D0 (en) * 1990-02-14 1991-02-27 Ici Plc Incorporation of desired groups into polymers,the polymers so produced and composition containing them
JPH0418172A (ja) * 1990-05-11 1992-01-22 Asahi Glass Co Ltd シリコーン系繊維処理剤
JPH0658507B2 (ja) * 1991-03-13 1994-08-03 工業技術院長 光学素子
JPH0971506A (ja) * 1995-06-27 1997-03-18 Pola Chem Ind Inc 架橋型シリコーン含有化粧料
US5952443A (en) * 1997-08-01 1999-09-14 Ppg Industries Ohio, Inc. Acetoacetate functional polysiloxanes
US6121404A (en) * 1998-07-06 2000-09-19 Dow Corning Corporation β-diketo functional organosilicon compounds
NO325853B1 (no) * 2004-04-16 2008-08-04 Nor X Ind As Polymer kommpound
DE102005056051A1 (de) * 2005-11-24 2007-05-31 Wacker Chemie Ag Verfahren zur Herstellung von beta-Ketocarbonyl-funktionellen Organosiliciumverbindungen
DE102005056050A1 (de) * 2005-11-24 2007-05-31 Wacker Chemie Ag Alpha-(beta-Ketocarbonyl)-funktionelle Organosiliciumverbindungen und deren Herstellung
DE102005058745A1 (de) * 2005-12-08 2007-06-14 Wacker Chemie Ag Enaminöle und Verfahren zu ihrer Herstellung
DE102006020816A1 (de) * 2006-05-04 2007-11-08 Wacker Chemie Ag Organosiliciumverbindungen, die beta-Ketoamidgruppen und über Enamin-Bindungen gebundene organische Polymere enthalten, und Verfahren zu ihrer Herstellung

Also Published As

Publication number Publication date
EP1852456A1 (fr) 2007-11-07
US20070260081A1 (en) 2007-11-08
CN101067024A (zh) 2007-11-07
KR100936414B1 (ko) 2010-01-12
DE102006020815A1 (de) 2007-11-08
DE502007000875D1 (de) 2009-07-30
KR20070108081A (ko) 2007-11-08
US7495119B2 (en) 2009-02-24
JP5044276B2 (ja) 2012-10-10
JP2007297630A (ja) 2007-11-15
CN101067024B (zh) 2012-08-08

Similar Documents

Publication Publication Date Title
EP1852456B1 (fr) Procédé pour la préparation de composés organosiliciques ß-cetocarbonyl-fonctionnalisé
EP0396130B1 (fr) Composés organosiliciques à fonction alcénoyloxy, leur préparation et leur emploi
EP1580215B1 (fr) Procédé de préparation d'organopolysiloxanes aminofonctionnels
EP1931719B1 (fr) Procede de production de polyorganosiloxanes
EP2129703A1 (fr) Procédé de production d'organopolysiloxanes
EP3728407B1 (fr) Procédé de production de siloxanes présentant des groupes oxamidoester
EP1954700B1 (fr) Procede pour preparer des composes d'organo-silicium a fonction beta-cetocarbonyle
EP2050777A2 (fr) Dispositif de support de tuyau dans une rainure d'un système de contrôle de température intégré dans une surface et son procédé
EP2260069B1 (fr) Composés organosiliciés cireux à fonction b-cétocarbonyle
EP2176320B1 (fr) Organopolysiloxanes présentant des groupes polyhydroxyamido et leur utilisation
EP0675150B1 (fr) Procédé de préparation de composés organosiliciques contenant des groupes carboxyliques
EP1541615B1 (fr) Procédé de préparation d'organopolysiloxanes à viscosité élevée
EP0503668B1 (fr) Composés organosiliciés contenant des groupes alkényles, leur fabrication et leur utilisation
EP0690062B1 (fr) Composés organosiliciques ayant des groupes furannyle
EP2029661B1 (fr) Procédé de fabrication d'organopolysiloxanes de poids moléculaire élevé
EP0639205B1 (fr) Copolymeres de siloxane comportant des groupes vinyloxy, leur fabrication et leur utilisation
EP0431609B1 (fr) Organopolysiloxanes contenant des groupes sulfosuccinates
EP2123697B1 (fr) Procédé de préparation de polysiloxanes organiques portant des groupes ammonium quaternaires
EP3411426B1 (fr) Procédé de production d'organopolysiloxanes contenant des groupes amino
DE19718470A1 (de) Verfahren zur Herstellung von Si-gebundene Wasserstoffatome aufweisenden Organosiliciumverbindungen
EP0538868B1 (fr) Composés organosiliciés comportant des groupes de sel de Bunte, leur procédé de préparation et leur utilisation
WO2018065070A1 (fr) Aminosiloxanes secondaires et son procédé de production

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20070419

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA HR MK YU

17Q First examination report despatched

Effective date: 20080318

AKX Designation fees paid

Designated state(s): BE DE FR GB NL

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB NL

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REF Corresponds to:

Ref document number: 502007000875

Country of ref document: DE

Date of ref document: 20090730

Kind code of ref document: P

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20100318

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20130418

Year of fee payment: 7

REG Reference to a national code

Ref country code: NL

Ref legal event code: V1

Effective date: 20141101

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20141101

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 10

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20170419

Year of fee payment: 11

Ref country code: GB

Payment date: 20170419

Year of fee payment: 11

Ref country code: DE

Payment date: 20170419

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20170419

Year of fee payment: 11

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 502007000875

Country of ref document: DE

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20180430

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20180419

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20181101

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20180419

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20180430

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20180430